Ingenines A and B, Two New Alkaloids from the Indonesian Sponge Acanthostrongylophora ingens

Abstract

As a continuation of the work on EtOAc fraction of the Indonesian sponge Acanthostrongylophora ingens, 2 new alkaloids: one pyrimidine-β-carboline alkaloid named ingenine A (2) and one pyrimidine-γ-carboline alkaloid named ingenine B (3), along with annomontine (1) were isolated. Their structures were unambiguously established on the basis of NMR spectroscopy (¹ H, ¹³C, ¹ H-¹ H COSY, HMQC, and HMBC) and mass spectral data. This is the first report of isolation pyrimidine-γ-carboline alkaloid from natural source. Compounds 1 and 3 showed pronounced cytotoxicity against the murine lymphoma L5178Y cancer cell line with ED₅₀ 7.8 and 9.1 μg/mL respectively, while compound 2 showed weak activity.

Key words

acanthostrongylophora ingens - pyrimidine-β-carboline - pyrimidine-γ-carboline - ingenine - cytotoxic activity

• References

• 1 Samoylenko V, Khan SI, Jacob MR et al. Bioactive (+)-manzamine A and (+)-8-hydroxymanzamine A tertiary bases and salts from Acanthostrongylophora ingens and their preparations. Nat Prod Commun 2009; 4: 185-192
• 2 Rao KV, Donia MS, Peng J et al. Manzamine B and E and ircinal A related alkaloids from an Indonesian Acanthostrongylophora sponge and their activity against infectious, tropical parasitic, and Alzheimer’s diseases. J Nat Prod 2006; 69: 1034-1040
• 3 Ibrahim SRM, Ebel RA, Ebel R et al. Alkaloids of the Annonaceae. Part 33. annomontine and methoxyannomontine, two new pyrimidine-β-carboline-type alkaloids from Annona montana. Nat Prod Commun 2008; 3: 175-178
• 4 Mohamed GA, Ibrahim SRM, Ross SA. New ceramides and isoflavone from the Egyptian Iris germanica L. Rhizomes. Phytochemistry Lett 2013; 6: 340-344
• 5 Ibrahim SRM. New chromone and triglyceride from Cucumis melo seeds. Nat Prod Commun 2014; 9: 205-208
• 6 Leboeuf M, Andre C, Forgacs P et al. Alkaloids of the Annonaceae. Part 33. annomontine and methoxyannomontine, two new pyrimidine-β-carboline-type alkaloids from Annona montana. J Chem Soc Perkin Trans 1982; 1: 1205-1208
• 7 Costa EV, Pinheiro MLB, de Souza ADL et al. Full NMR analysis of annomontine, methoxyannomontine and N-hydroxyannomontine pyrimidine-β-carboline alkaloids. Magn Reson Chem 2008; 46: 69-74
• 8 Corbally RP, Mehta LK, Parrick J et al. Experimental and calculated ¹³C chemical shifts for α-, β-, γ- and δ-carbolines. Magn Reson Chem 2000; 38: 1034-1036
• 9 Guo-wei L, Bai-ping Y, De-xi L. The isolation and structural determination of γ-harmane from the seed of Peganum harmala L. Acta Bot Sinica 1989; 31: 393-397
• 10 Ivachtchenko AV, Frolov EB, Mitkin OD et al. Synthesis and biological evaluation of novel γ-carboline analogues of Dimebon as potent 5-HT6 receptor antagonists. Bioorg Med Chem Lett 2009; 19: 3183-3187